Tuning the coordination number of hydroxypyridonate-based gadolinium complexes: Implications for MRI contrast agents

被引:38
作者
Pierre, VC
Botta, M
Aime, S
Raymond, KN [1 ]
机构
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
[2] Univ Piemonte Orientale, Dipartimento Sci Ambiente & Vita, I-15100 Alessandria, Italy
[3] Univ Turin, Dipartimento Chim, IFM, I-10125 Turin, Italy
关键词
D O I
10.1021/ja057805x
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Eight-coordinate hydroxypyridinone/terephthalamide GdIII complexes display high relaxivities due to their two inner sphere water molecules. This relaxivity can be further increased by functionalizing the terephthalamide moiety with an amine. A significant hydrogen bonding interaction between the amine and another water molecule close to the GdIII apparently facilitates its coordination on the open site of the metal. The resulting nine-coordinate complex has three inner sphere water molecules, while maintaining high stability and fast ligand exchange rates. Copyright © 2006 American Chemical Society.
引用
收藏
页码:5344 / 5345
页数:2
相关论文
共 10 条
[1]   Gadolinium(III) chelates as MRI contrast agents: Structure, dynamics, and applications [J].
Caravan, P ;
Ellison, JJ ;
McMurry, TJ ;
Lauffer, RB .
CHEMICAL REVIEWS, 1999, 99 (09) :2293-2352
[2]   Mixed hydroxypyridinonate ligands as iron chelators [J].
Cohen, SM ;
O'Sullivan, B ;
Raymond, KN .
INORGANIC CHEMISTRY, 2000, 39 (19) :4339-4346
[3]   Syntheses and relaxation properties of mixed gadolinium hydroxypyridinonate MRI contrast agents [J].
Cohen, SM ;
Xu, JD ;
Radkov, E ;
Raymond, KN ;
Botta, M ;
Barge, A ;
Aime, S .
INORGANIC CHEMISTRY, 2000, 39 (25) :5747-5756
[4]   Structural, luminescence, and NMR studies of the reversible binding of acetate, lactate, citrate, and selected amino acids to chiral diaqua ytterbium, gadolinium, and europium complexes [J].
Dickins, RS ;
Aime, S ;
Batsanov, AS ;
Beeby, A ;
Botta, M ;
Bruce, J ;
Howard, JAK ;
Love, CS ;
Parker, D ;
Peacock, RD ;
Puschmann, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) :12697-12705
[5]   Toward optimized high-relaxivity MRI agents: The effect of ligand basicity on the thermodynamic stability of hexadentate hydroxypyridonate/catecholate gadolinium(III) complexes [J].
Doble, DMJ ;
Melchior, M ;
O'Sullivan, B ;
Siering, C ;
Xu, JD ;
Pierre, VC ;
Raymond, KN .
INORGANIC CHEMISTRY, 2003, 42 (16) :4930-4937
[6]   Next generation, high relaxivity gadolinium MR1 agents [J].
Raymond, KN ;
Pierre, VC .
BIOCONJUGATE CHEMISTRY, 2005, 16 (01) :3-8
[7]   In vivo evaluation of gadolinium hydroxypyridonate chelates: Initial experience as contrast media in magnetic resonance imaging [J].
Thompson, MK ;
Misselwitz, B ;
Tso, LS ;
Doble, DMJ ;
Schmitt-Willich, H ;
Raymond, KN .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (11) :3874-3877
[8]   A highly stable gadolinium complex with a fast, associative mechanism of water exchange [J].
Thompson, MK ;
Botta, M ;
Nicolle, G ;
Helm, L ;
Aime, S ;
Merbach, AE ;
Raymond, KN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (47) :14274-14275
[9]   GADOLINIUM COMPLEX OF TRIS[(3-HYDROXY-1-METHYL-2-OXO-1,2-DIDEHYDROPYRIDINE-4-CARBOXAMIDO)ETHYL]AMINE - A NEW CLASS OF GADOLINIUM MAGNETIC-RESONANCE RELAXATION AGENTS [J].
XU, J ;
FRANKLIN, SJ ;
WHISENHUNT, DW ;
RAYMOND, KN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (27) :7245-7246
[10]   Gadolinium(III) 1,2-hydroxypyridonate-based complexes: Toward MRI contrast agents of high relaxivity [J].
Xu, J ;
Churchill, DG ;
Botta, M ;
Raymond, KN .
INORGANIC CHEMISTRY, 2004, 43 (18) :5492-5494